Ethanol → 1-(benzenesulfonyl)-1H-indole-5-carbaldehyde

반응식

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](C=O)=[CH:2]1.[OH-].[K+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:24]([OH:26])C>>[C:14]1([S:20]([N:1]2[C:9]3[C:4](=[CH:5][C:6]([CH:24]=[O:26])=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

반응물 4

HCID 702Ethanol

HCID 7369Benzenesulfonyl chloride

HCID 10256Indole-3-Carboxaldehyde

HCID 14797Potassium Hydroxide

생성물 1

HCID 177503871-(benzenesulfonyl)-1H-indole-5-carbaldehyde수율 32.6%

실험 절차

To a solution of indole-3-carboxaldehyde (100 mmol) in ethanol (500 mL) at room temperature was added potassium hydroxide (110 equiv), the mixture was stirred until total solubilization. The ethanol was completely removed in vacuum and acetone (250 mL) added followed by benzenesulfonyl chloride (110 equiv). The precipitate was filtered off and the filtrate was concentrated and recrystallized from methanol to give a white solid. Yield: 32.6% 1H NMR (500 MHz, CDCl3) δ 10.17 (s, 1H), 8.25-8.39 (m, 2H), 7.97-8.09 (m, 3H), 7.69 (t, J=7.33 Hz, 1H), 7.59 (t, J=7.5 Hz, 2H), 7.39-7.54 (m, 2H). MS (ESI) calcd for C15H11NO3S 285.1. found 286.0 [M+H]+.